Oxidation colorants for keratin fibers

Details Oxidation colorants for keratin fibers Oxidation colorants for keratin fibers

1992-11-19

2004-04-13

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S405000, C008S406000, C008S408000, C008S410000, C008S416000, C008S421000, C008S423000

Reexamination Certificate

active

06719811

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to the use of indoline derivatives, more particularly 5,6-dihydroxyindolines, as an oxidation dye precursor for the production of oxidative dyeing compositions for keratin fibers, more particularly for human hair.
STATEMENT OF RELATED ART
Natural hair dyes, so-called melanins, are formed during their biosynthesis by the oxidative polymerization of 5,6-dihydroxyindole. Accordingly, numerous attempts have been made in the past to use 5,6-dihydroxyindole as a reactive dye precursor in the dyeing of hair. Unfortunately, 5,6-dihydroxyindole is extremely unstable both in free form and in the form of its salts in aqueous solution and, in the presence of atmospheric oxygen, very quickly forms insoluble, colored oxidation and polymerization products which can no longer be fixed to the hair. Accordingly, all attempts to use 5,6-dihydroxyindole itself or its salts in dye preparations have led to unsatisfactory and commercially unusable hair dyes.
DESCRIPTION OF THE INVENTION
A new and surprising possibility has now been found for producing natural hair colors with melanin dyes via a 5,6-dihydroxyindole formed “in situ” without any of the stability problems typical of 5,6-dihydroxyindole.
SUMMARY OF THE INVENTION
The present invention relates to the use of indolines corresponding to formula I:
in which R
1
, R
2
, R
3
, R
4
, and R
5
independently of one another represent hydrogen or C
1-4
alkyl groups; or R
4
and R
5
together with the oxygen atoms to which they are attached may represent an alkylenedioxy group containing 1 to 4 carbon atoms, or salts thereof as oxidation dye precursors for the generation of oxidative dyeings.
DESCRIPTION OF PREFERRED EMBODIMENTS
5,6-Dihydroxyindoline, i.e. the indoline derivative corresponding to formula I, when R
1
, R
2
, R
3
, R
4
, and R
5
are hydrogen, is particularly suitable because it forms 5,6-dihydroxyindole and also melanin dye during the oxidation. However, it is also known that derivatives of 5,6-dihydroxyindole form dyes similar to melanin under oxidation conditions. Accordingly, the alkyl-substituted indolines corresponding to formula I, preferably those in which one of the groups R
1
, R
2
and R
3
is a methyl group and the others are hydrogen, are suitable for use as oxidation dye precursors for the production of storable dye preparations.
By virtue of the chemical similarity of the melanin dyes formed from the indolines to be used in accordance with the invention to the natural melanin dye, the dye preparations produced therewith can be expected to show favorable toxicological and dermatological behavior. Above all, however, particularly natural color tones in the mid-blond to mid-brown range with high fastness to light, mechanical friction, chemical treatment, for example with reducing cold-wave preparations, and to washing with surfactant solutions are obtained.
5,6-Dimethoxyindoline and 5,6-dihydroxyindoline are known from the literature, their production being described, for example, in
J. Chem. Soc
. (C), 1967, pages 1424 to 1427. The alkyl-substituted indolines corresponding to formula I can be similarly prepared from the correspondingly substituted 5,6-dihydroxyindoles or alkoxyindoles by catalytic hydrogenation. Another process for the production of 5,6-dihydroxyindolines from 5,6-dimethoxyindoles by reduction with sodium cyanoborohydride and elimination of the methoxy groups in concentrated hydrochloric acid is described in
Journal of Medicinal Chemistry
, 1978, Vol. 21, No. 6, page 553.
The indolines of formula I to be used in accordance with the invention are preferably used as sole oxidation dye precursors. They may be used in free form or in the form of their salts, preferably as hydrochlorides, hydrobromides, sulfates, phosphates, acetates, propionates, lactates or citrates.
However, other known oxidation dye precursors and, optionally, known substantive dyes may also be used together with the indolines corresponding to formula I for modifying the color tones.
In particular, it has been found that the indolines corresponding to formula I and also their salts are also eminently suitable for use as color modifiers in oxidation hair dyes containing typical primary intermediate compounds.
Accordingly, the present invention also relates to hair dyes containing oxidation dye precursors in a carrier, characterized in that they contain indolines corresponding to formula I or salts thereof as color modifiers together with the primary intermediate compounds typically used for oxidation hair dyes. The indolines corresponding to formula I modify the colors obtainable with the primary intermediate compounds alone by self-coupling and lead to intensive, brilliant dark-brown to blue-black tones.
The hair dyes according to the invention preferably contain a mildly basic carrier.
The typical primary intermediate components used may be any of the compounds known for this purpose. Those of the aromatic or heterocyclic amino compound type are preferred. Suitable primary intermediate compounds of this type are, for example, p-phenylenediamine, p-tolylenediamine, 2-chloro-p-phenylenediamine, N-methyl-p-phenylenediamine, N,N-diethyl-p-phenylenediamine, N-(&bgr;-hydroxyethyl)-p-phenylenediamine, N,N-dimethyl-p-phenylenediamine, N,N-bis-(&bgr;-hydroxyethyl)-p-phenylenediamine, 2,5-diaminobenzyl alcohol and other compounds of the type mentioned which may also contain one or more NH
2
groups, NHR groups, or NR
2
groups, in which R represents C
1-4
alkyl groups or C
2-4
hydroxyalkyl groups, and also p-aminophenols, 1-amino-4-naphthol or tetraaminopyrimidines, for example 2,4,5,6-tetraaminopyrimidine or 2-dimethylamino-4,5,6-triaminopyrimidine, diaminopyrimidines, or 1-phenyl-3-carboxamido-4-amino-5-pyrazolone.
Where the indolines corresponding to formula I are used as color modifiers for modifying the color tone of the primary intermediate compounds mentioned, they are used in quantities of 0.1 to 10 millimole per 100 g of the hair dye. They are typically used in substantially molar quantities, based on the primary intermediate compounds used. Although it has proved to be advisable to use molar quantities, there is no disadvantage in using an excess of individual oxidation dye precursors.
The indolines corresponding to formula I do not have to be individual chemical compounds, instead they may also be mixtures of the indolines, corresponding to formula I or their salts to be used in accordance with the invention.
To produce oxidative dyeing compositions, the oxidation dye precursors are incorporated in a suitable carrier. Such carriers are, for example, creams, emulsions, gels, or even surfactant-containing foaming solutions (shampoos), foam aerosols, or other preparations suitable for application to the hair. The carriers in question contain formulation and dyeing aids which increase the stability of the preparations and improve the result of dyeing. Such additives are, primarily, surface-active agents, for example
soaps, more particularly the alkali metal or alkanolamine soaps of linear C
12-18
fatty acids, more particularly oleic acid,
anionic surfactants, for example fatty alcohol sulfates and fatty alcohol polyglycol ether sulfates, alkane sulfonates, &agr;-olefin sulfonates, or oleic acid sulfonates, preferably in the form of their alkali metal, ammonium, or alkanolammonium salts
cationic surfactants, for example alkyl (C
12-18
) trimethyl ammonium chloride, alkyl (C
12
-
18
) dimethyl benzyl ammonium salts, cetyl pyridinium chloride, 2-hydroxydodecyl hydroxyethyl dimethyl ammonium chloride
zwitterionic surfactants such as, for example, alkyl (C
12-18
) dimethyl ammonium glycinate, coconut oil acylaminopropyl dimethyl ammonium glycinate or imidazolinium betaines
amphoteric surfactants such as, for example, N-dodecylaminoacetic acid, N-cetylaminopropionic acid, &Ugr;-laurylaminobutyric acid and
nonionic surfactants, more particularly adducts of 5 to 30 mol ethylene oxide with fatty alcohols, with alkylphenols, with fatty acids, with fatty acid alkanolamides, with fatty acid partial gly

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